The Montreal Canadiens visit the Toronto Maple Leafs on September 29 in a preseason opener that features Ivan Demidov’s new extension and a reshaped Leafs coaching staff.
The Montreal Canadiens and Toronto Maple Leafs open their 2026-27 preseason schedules against each other on September 29 at Scotiabank Arena, with both teams looking to set a tone after eventful offseasons. Montreal arrives as the Atlantic Division’s second-place finisher from last season, while Toronto sits eighth in the same division after a turbulent summer of front-office and coaching changes. The edge in this exhibition matchup likely belongs to the Canadiens, who have more continuity and a clearer identity, but the Leafs will be eager to show their new-look staff can spark a turnaround.
Montreal Canadiens: Building Around Demidov
The Canadiens locked up rookie standout Ivan Demidov to an eight-year contract extension, a move that signals their commitment to a young core. Demidov was runner-up for Calder Trophy honors last season, and his presence gives Montreal a dynamic offensive threat. The team also traded veteran forward Brendan Gallagher to Vancouver for future considerations, ending a 14-season tenure. That move opens ice time for younger players and shifts the leadership dynamic. Montreal finished second in the Atlantic last season, setting high expectations. With training camp underway, the Canadiens will use this preseason game to evaluate roster battles and integrate new free-agent additions. The absence of Gallagher’s net-front presence is a storyline to watch, but Demidov’s extension provides a boost.
Toronto Maple Leafs: New Faces, New Direction
The Maple Leafs enter the preseason with a dramatically reshaped front office and coaching staff. Assistant general manager Hayley Wickenheiser was fired as part of a broader purge, and the team hired Senators legend Daniel Alfredsson as associate coach, a move that adds a fresh perspective but also raises questions about organizational direction. Toronto finished eighth in the Atlantic last season, a disappointing result for a team with playoff aspirations. The Leafs will be looking to their new staff to implement systems and get the most out of their roster. No. 1 overall pick Gavin McKenna has set rookie season goals and is a player to watch, though his roster status is unconfirmed. The blue line and goaltending remain question marks, and this preseason opener will be an early test of how the team responds.
Head-to-Head: X-Factors and Key Matchups
This preseason clash features several intriguing storylines. Demidov’s offensive skill will test a Leafs defense that is still finding its identity. Toronto’s new coaching staff, led by Alfredsson, will be eager to implement their system against a quality opponent. For Montreal, the absence of Gallagher means other forwards must step up in leadership and net-front presence. Special teams could be a factor, as both teams work on new units. The goaltending battle is also worth monitoring, as both teams have question marks in net.
- Ivan Demidov’s debut under his new contract
- Daniel Alfredsson’s first game as Leafs associate coach
- Life after Brendan Gallagher for Montreal
- Gavin McKenna’s preseason performance
- Goaltending depth for both teams
Prediction
Expect a competitive but sloppy preseason game as both teams use this to evaluate talent. The Canadiens’ continuity and Demidov’s firepower give them the edge. Look for Montreal to win a high-scoring affair, with the Leafs showing flashes but struggling to contain Demidov and the Canadiens’ top line. Prediction: Canadiens 4, Maple Leafs 3 in a shootout.
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